4-(Furan-2-ylmethoxy)benzene-1,2-dicarbonitrile

In the title compound, C13H8N2O2, prepared from furfuryl alcohol and 4-nitrophthalonitrile in the presence of potassium carbonate in dimethylformamide, the furan and benzene rings are oriented at a dihedral angle of 53.45 (9)°. In the crystal, weak C—H⋯O and C—H⋯N hydrogen bonds link the molecules into a three-dimensional network.

In the title compound, C 13 H 8 N 2 O 2 , prepared from furfuryl alcohol and 4-nitrophthalonitrile in the presence of potassium carbonate in dimethylformamide, the furan and benzene rings are oriented at a dihedral angle of 53.45 (9) . In the crystal, weak C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds link the molecules into a three-dimensional network.

Comment
Phthalonitriles are used for preparing symmetrically and unsymmetrically substituted phthalocyanine complexes (Leznoff & Lever, 1996). Phthalocyanines have currently been the topic of research because of their wide application fields, such as thin film fabrication, organic pigments, chemical sensors, electrochromic display devices, molecular epitaxic deposition and composites, liquid crystals, photovoltaic cells self-assembled materials. The fundamental optical and electronic properties of these materials are explained and their potential in non-linear optics, optical data storage, electronic sensors, xerography, solar energy conversion, nuclear chemistry, molecular magnetism, electrochromic displays and heterogeneous catalysis is evaluated by McKeown (1998). The title compound was synthesized and its crystal structure is reported herein.
In the title compound, (Fig. 1), the bond lengths are close to standard values (Allen et al., 1987). In the crystal, weak intermolecular C-H···O and C-H···N hydrogen bonds (Table 1) link the molecules into a threedimensional network (Fig. 2).

Experimental
For the preparation of the title compound, furfuryl alcohol (1.49 g, 15.2 mmol) and 4-nitrophthalonitrile (2.64 g, 15.2 mmol) were heated at 358 K in dry DMF (15 ml) with stirring under argon atmosphere. Then, dry fine powdered potassium carbonate (6.00 g, 43.47 mmol) was added in portions (14 × 3.1 mmol) every 10 min. The mixture was heated for a further 24 h. After cooling, the mixture was added into ice-water (200 g). The product was filtered off and washed with NaOH solution (10%) and water until the filtrate was neutral. Recrystallization from ethanol gave a white product (yield: 1.25 g, 55.85%). Single crystals suitable for X-ray diffraction mesurement was obtained by slow evaporation of the solution in ethanol (m.p. 385-387 K).

Refinement
The C-bound H-atoms were positioned geometrically with C-H = 0.95 Å and 0.99 Å, for aromatic and methylene H-atoms, respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2 U eq (C). Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.